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$49+ Cheap flights from Kentucky to Chicago (CHI)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/22. Fares are subject to change and may not be available on all flights or dates of travel.
SDF — CHI
Aug 4 — Aug 111
Mon 8/4
Mon 8/11
1 adult, Economy
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Cheap flight deals from Kentucky to Chicago

Keep the following information in mind while searching for Kentucky to Chicago flight deals. Data was last updated July 30, 2025.

Round-trip from

$79
(CheapOair)

One-way from

$49
(American Airlines)

Popular in

March

Cheapest in

April

Average price

$280

Good round-trip deal

$144 or less

Good one-way deal

$206 or less
From Kentucky to Chicago (CHI)
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One-way flight from Kentucky to Chicago (CHI)
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High demand for flights, 0% potential price rise
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Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
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Average for round-trip flights in July 2025
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Price to beat on a round-trip flight from Kentucky to Chicago (CHI).
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Price to beat on a one-way flight from Kentucky to Chicago (CHI).
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Find flight deals from Kentucky to Chicago

Cheapest flights from Kentucky to Chicago
Explore the most affordable flight options available from Kentucky to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 30, 2025.

This Mytrip deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/41:23 pmTYS - MDW
Nonstop1h 33mAllegiant Air
Fri 8/82:46 pmMDW - TYS
Nonstop1h 26mAllegiant Air
Deal found 7/30$79
This CheapOair deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/56:10 amBNA - ORD
1 stop12h 13mSpirit Airlines
Mon 11/104:01 pmORD - BNA
Nonstop1h 40mSpirit Airlines
Deal found 7/28$79
This Gotogate deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/83:07 pmBNA - ORD
Nonstop2h 04mFrontier
Mon 8/1112:35 pmORD - BNA
Nonstop1h 39mFrontier
Deal found 7/29$83
This American Airlines deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/206:44 amSDF - ORD
Nonstop1h 46mAmerican Airlines
Wed 8/2011:49 amORD - SDF
Nonstop1h 26mAmerican Airlines
Deal found 7/30$97
This Southwest deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/27:15 amSDF - MDW
Nonstop1h 20mSouthwest
Tue 9/24:10 pmMDW - SDF
Nonstop1h 15mSouthwest
Deal found 7/29$97
This Southwest deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/235:50 amBNA - MDW
Nonstop1h 35mSouthwest
Sat 8/232:50 pmMDW - BNA
Nonstop1h 25mSouthwest
Deal found 7/29$97
This American Airlines deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/139:15 amBNA - ORD
Nonstop1h 46mAmerican Airlines
Sat 9/2010:11 amORD - BNA
Nonstop1h 31mAmerican Airlines
Deal found 7/30$97
This Southwest deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/234:30 pmBNA - ORD
1 stop5h 30mSouthwest
Tue 8/263:10 pmORD - BNA
Nonstop1h 35mSouthwest
Deal found 7/29$107
This Orbitz deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/55:45 amBNA - ORD
1 stop11h 54mMultiple Airlines
Sun 9/712:53 pmORD - BNA
Nonstop1h 43mMultiple Airlines
Deal found 7/29$109
This United Airlines deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/169:05 amSDF - ORD
Nonstop1h 38mUnited Airlines
Wed 9/247:26 amORD - SDF
Nonstop1h 36mUnited Airlines
Deal found 7/29$157
This Southwest deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/235:50 amSDF - ORD
1 stop7h 00mSouthwest
Mon 8/257:30 amORD - SDF
1 stop6h 20mSouthwest
Deal found 7/29$175
This American Airlines deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/202:47 pmCVG - ORD
Nonstop1h 30mAmerican Airlines
Sat 8/238:47 amORD - CVG
Nonstop1h 27mAmerican Airlines
Deal found 7/30$176

Cheapflights Fare Finder

 
Customize your flight search to find flights from Kentucky to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated July 30, 2025.
Use the filters below to find and compare flights from Kentucky to Chicago that are best for you.

Fly from

Kentucky

Fly to

Chicago

Route

Depart

Return

Price

NashvilleChicago

BNA - ORD

BNAORD

Nashville Intl

Wed 11/5

6:10 am-6:23 pm

1 stop12h 13m

Chicago O'Hare Intl

Mon 11/10

4:01 pm-5:41 pm

Nonstop1h 40m

$79

KnoxvilleChicago

TYS - MDW

TYSMDW

Knoxville McGhee Tyson

Fri 8/22

2:29 pm-3:02 pm

Nonstop1h 33m

Chicago Midway

Mon 8/25

3:52 pm-6:20 pm

Nonstop1h 28m

$80

NashvilleChicago

BNA - ORD

BNAORD

Nashville Intl

Fri 9/12

3:21 pm-5:26 pm

Nonstop2h 05m

Chicago O'Hare Intl

Sun 9/14

12:53 pm-2:36 pm

Nonstop1h 43m

$88

LouisvilleChicago

SDF - ORD

SDFORD

Louisville Intl

Wed 8/20

6:44 am-7:30 am

Nonstop1h 46m

Chicago O'Hare Intl

Wed 8/20

11:49 am-2:15 pm

Nonstop1h 26m

$97

LouisvilleChicago

SDF - MDW

SDFMDW

Louisville Intl

Tue 9/2

7:15 am-7:35 am

Nonstop1h 20m

Chicago Midway

Tue 9/2

4:10 pm-6:25 pm

Nonstop1h 15m

$97

NashvilleChicago

BNA - MDW

BNAMDW

Nashville Intl

Sat 8/23

5:50 am-7:25 am

Nonstop1h 35m

Chicago Midway

Sat 8/23

2:50 pm-4:15 pm

Nonstop1h 25m

$97

NashvilleChicago

BNA - ORD

BNAORD

Nashville Intl

Sat 9/13

9:15 am-11:01 am

Nonstop1h 46m

Chicago O'Hare Intl

Sat 9/20

10:11 am-11:42 am

Nonstop1h 31m

$97

NashvilleChicago

BNA - ORD

BNAORD

Nashville Intl

Sat 8/23

4:30 pm-10:00 pm

1 stop5h 30m

Chicago O'Hare Intl

Tue 8/26

3:10 pm-4:45 pm

Nonstop1h 35m

$107

NashvilleChicago

BNA - ORD

BNAORD

Nashville Intl

Fri 9/5

5:45 am-5:39 pm

1 stop11h 54m

Chicago O'Hare Intl

Sun 9/7

12:53 pm-2:36 pm

Nonstop1h 43m

$109

LouisvilleChicago

SDF - ORD

SDFORD

Louisville Intl

Tue 9/16

9:05 am-9:43 am

Nonstop1h 38m

Chicago O'Hare Intl

Wed 9/24

7:26 am-10:02 am

Nonstop1h 36m

$157

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/28

Showing 1-10 of 60 results
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Best time to book a flight from Kentucky to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Kentucky with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Kentucky to Chicago

What is the cheapest month to book a flight from Kentucky to Chicago?

Currently, August is the cheapest month in which you can book a flight from Kentucky to Chicago (average of $245). Flying from Kentucky to Chicago in March is currently the most expensive (average of $321). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from KY to CHI?

Find hourly flight availability from Kentucky to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated July 30, 2025.

When flying from Kentucky to Chicago, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Weekly flight availability from Kentucky to Chicago

Explore weekly flight availability from Kentucky to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated July 30, 2025.

The most flights from USKY to CHI are scheduled on a Monday (45 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (16 on average).

How much does it cost to fly round-trip from Kentucky to Chicago?

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated July 30, 2025.
Get a feel of what it's like to fly with Southwest, Delta, and United Airlines from Kentucky to Chicago by reading reviews from past customers. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,241 reviews

Overall

8.0

Crew

8.6

Food

7.0

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Southwest
8.0
Very good
4,241 reviews
Southwest
8.0
Very good
4,241 reviews

Overall

8.0

Crew

8.6

Food

7.0

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Delta
8.0
Very good
7,980 reviews
Southwest
8.0
Very good
4,241 reviews

Overall

8.0

Crew

8.6

Food

7.0

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
United Airlines
7.4
Good
8,896 reviews
Southwest
8.0
Very good
4,241 reviews

Overall

8.0

Crew

8.6

Food

7.0

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,241 reviews

Overall

8.0

Crew

8.6

Food

7.0

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Allegiant Air
7.2
Good
703 reviews
Southwest
8.0
Very good
4,241 reviews

Overall

8.0

Crew

8.6

Food

7.0

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.

Related info for your journey

Find useful and relevant information for your journey from Kentucky to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What are the cheapest airlines to fly from Kentucky to Chicago one-way?

    To fly one-way, consider booking your trip with American Airlines, which is currently one of the cheapest options available, starting at $49. Southwest flights start at $49 while deals on Spirit Airlines start at $50 one-way.

  • What are the most popular routes from Kentucky to Chicago?

    The most popular flight routes from Kentucky to Chicago are Nashville Intl - Chicago O'Hare Intl, Cincinnati Cinci./N. Kentucky - Chicago O'Hare Intl and Louisville Intl - Chicago O'Hare Intl.

  • What are the most reliable airlines from Kentucky to Chicago?

    Before booking your flight to Chicago from Kentucky, check out the most reliable airlines to get you to your destination on time: Japan Airlines (93%), Republic Airways (85%), Copa Airlines( 85%).

  • What are the cheapest flights from Kentucky to Chicago?

    On average you can expect to pay $1,521 for a flight from Kentucky to Chicago. The cheapest flight overall is $89 while the most popular route, (Nashville Intl - Chicago O'Hare Intl) is currently priced at $59.

  • Can I find deals for flights from Kentucky to Chicago that include hotel bookings?

    Yes. In addition to deals on Kentucky to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Kentucky to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Kentucky to Chicago.

  • Can I find deals for business class flights from Kentucky to Chicago?

    Yes. Cheapflights offers flight deals from Kentucky to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Kentucky to Chicago?

    Currently, August is the cheapest month in which you can book a flight from Kentucky to Chicago (average of $245). Flying from Kentucky to Chicago in March is currently the most expensive (average of $321). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Valparaiso
Chesterton

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Alternative routes for Kentucky to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
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Top 4 airlines flying from Kentucky to Chicago

Discover the top 4 airlines that operate flights from Kentucky to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated July 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$97Average$264FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$97Average$275FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$106Average$280FlexibilityNo cancel feeOn-time69%
ContourCheapest$113Average$143FlexibilityNo cancel feeOn-timeN/A

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